Vacation rentals in Woolford

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Top-rated vacation rentals in Woolford

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Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 161 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Jan 26 – Feb 2

G$25,829 GYD per night

Guest favorite

Cottage in Cambridge

4.98 out of 5 average rating, 108 reviews

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Two miles from a main road, and our closest neighbor is across a cove, our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

Mar 10 – 17

G$44,238 GYD per night

Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 497 reviews

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette 5 min away from Blackwater Refuge! It is an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! Staying the cabin will make your visit even more memorable!The Tiny Cabin is now located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

Aug 6 – 13

G$17,583 GYD per night

Guest favorite

Guest suite in Cambridge

4.95 out of 5 average rating, 266 reviews

Oakley Suite

5 minute walk to restaurants and shops, 3 min.to the water. Ideal setting with lovely rear patio and garden with entrance to private family room. Stairs to upper level with 2 very large and private guest rooms. Landing at top of steps presents a convenience station with Keurig, microwave, and mini fridge. This Suite is completely private and includes 2 bedrooms, bath, family room, convenience station, and rear patio, all for one price! 1st floor Owners Suite available as well for a total of 8 !

Dec 1 – 8

G$31,119 GYD per night

Guest favorite

Home in Cambridge

4.99 out of 5 average rating, 139 reviews

Sunset Breezes - quiet waterfront retreat

Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Jan 9 – 16

G$88,523 GYD per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 192 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

Mar 23 – 30

G$18,547 GYD per night

Guest favorite

Loft in Lusby

5.0 out of 5 average rating, 310 reviews

Coastal Treetop Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction stove, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

Dec 6 – 13

G$26,892 GYD per night

Guest favorite

Apartment in Church Creek

4.97 out of 5 average rating, 371 reviews

Church Creek Natures' Rest

Nature's Rest is ideally located, just minutes to Blackwater Wildlife Refuge The Harriet Tubman Museum, as well as boat ramps for easy access to the Chesapeake Bay and it's tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

Feb 6 – 13

G$27,427 GYD per night

Guest favorite

Home in Woolford

4.93 out of 5 average rating, 118 reviews

Waterfront Getaway with Dock

Bicyclist's and outdoorsman's dream! Beautiful rancher on two waterfront acres just 4 miles from Blackwater Wildlife Refuge and Harriet Tubman National Park. 10 minute drive from downtown, the Hyatt, and the Ironman starting point as well. Ironman and Eagleman races actually pass right by! Bright, sunny, and newly renovated, it's a great place to hang your hat after a day of hunting, fishing, bicycling, or triatholon-ing! Or just take a weekend to relax on the water!

Oct 25 – Nov 1

G$47,222 GYD per night

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 313 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Oct 23 – 30

G$18,371 GYD per night

Guest favorite

Tiny home in Cambridge

4.99 out of 5 average rating, 154 reviews

Blackwater Refuge House on The Farm, water access

The Little House on The Farm is located on a beautiful family farm in rural Dorchester County! Located just 1.5 miles from the Blackwater Wildlife Refuge and Harriet Tubman National Park, This space is quaint,yet provides all the basics for a cozy welcoming getaway! Bring your bikes and cycle to the refuge and kayak in the Blackwater River. Kitchen is fully stocked for cooking. Coffee, tea and basic condiments and all linens and towels are provided.

Jun 11 – 18

G$21,680 GYD per night

Superhost

Home in Cambridge

4.89 out of 5 average rating, 111 reviews

Dorothy's Chesapeake Delight

810 Seabreeze Rd is a quiet cozy retreat located on Brooks Creek off the little Choptank river directly across from the ragged point county boat ramp and dock. Guests are welcome to bring their boat. The house's private dock is just a quarter mile from the public marina. This house is the perfect place for boating, kayaking, paddle boarding, fishing, swimming, crabbing or just relaxing watching the sunset over the historic little Choptank river.

Sep 26 – Oct 3

G$35,719 GYD per night